JP4577205B2 - シクロヘキサノンオキシムの製造方法 - Google Patents
シクロヘキサノンオキシムの製造方法 Download PDFInfo
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- JP4577205B2 JP4577205B2 JP2005364436A JP2005364436A JP4577205B2 JP 4577205 B2 JP4577205 B2 JP 4577205B2 JP 2005364436 A JP2005364436 A JP 2005364436A JP 2005364436 A JP2005364436 A JP 2005364436A JP 4577205 B2 JP4577205 B2 JP 4577205B2
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- cyclohexanone
- ammonia
- hydrogen peroxide
- reaction mixture
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- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 title description 37
- 238000004519 manufacturing process Methods 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 78
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 75
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 73
- 229910021529 ammonia Inorganic materials 0.000 claims description 39
- 239000011541 reaction mixture Substances 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 13
- 239000007791 liquid phase Substances 0.000 claims description 9
- 238000005192 partition Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000002994 raw material Substances 0.000 description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000012489 doughnuts Nutrition 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
この例で用いた反応装置は、図2に概略で示されるとおりである。すなわち、SUS316製の攪拌槽型反応器1に、シクロヘキサノン2’を6.83部、60%過酸化水素水3’を4.44部、及びアンモニア4’を2.23部の割合で、それぞれ供給口2a、3a及び4aから供給し、さらに含水t−ブチルアルコール(水12%)を23.6部の割合で供給しながら、抜き出し口1aからフィルターを介して反応混合物の液相1’を抜き出すことにより、温度85℃、圧力0.35MPa(絶対圧)、滞留時間1.5時間の条件で連続式反応を行った。この間、反応器1内の反応混合物中には、30g/Lの濃度でチタノシリケート(Polimeri Europa社製)を存在させた。反応開始から20時間後に抜き出した反応混合物の液相1’を分析した結果、シクロヘキサノンの転化率は99.8%、シクロヘキサノンオキシムの選択率は99.4%であり、シクロヘキサノンオキシムの収率は99.2%であった。また、アンモニアの濃度は2%であった。
2……シクロヘキサノン供給管、
3……過酸化水素供給管、
4……アンモニア供給管、
1a…反応混合物抜き出し口、
2a…シクロヘキサノン供給口、
3a…過酸化水素供給口、
4a…アンモニア供給口、
1’…反応混合物、
2’…シクロヘキサノン、
3’…過酸化水素、
4’…アンモニア、
5……隔壁、
6……攪拌翼。
Claims (4)
- 反応器内にチタノシリケート触媒が分散した反応混合物を存在させ、この中にシクロヘキサノン、過酸化水素及びアンモニアをそれぞれシクロヘキサノン供給口、過酸化水素供給口及びアンモニア供給口から供給して、連続式反応によりシクロヘキサノンオキシムを製造する方法であって、上記反応混合物は循環流を形成しており、かつ、シクロヘキサノン供給口を基準として、該循環流の下流側に、過酸化水素供給口及びアンモニア供給口がこの順に設けられており、さらに、シクロヘキサノン供給口、過酸化水素供給口及びアンモニア供給口のうち、アンモニア供給口が最下部に設けられ、最上部に過酸化水素供給口が設けられ、シクロヘキサノン供給口がアンモニア供給口及び過酸化水素供給口の間に設けられていることを特徴とする方法。
- 前記反応混合物の液相中のアンモニア濃度が1重量%以上である請求項1に記載の方法。
- 前記反応器内に、攪拌翼と、該攪拌翼を囲むように円筒形の隔壁が設けられている請求項1又は2に記載の方法。
- アンモニア供給口が前記隔壁の下側に設けられ、過酸化水素供給口が前記隔壁の上側に設けられ、シクロヘキサノン供給口が前記隔壁の外側に設けられ、さらに、前記隔壁の内側に反応混合物の下降流が形成され、前記隔壁の外側に反応混合物の上昇流が形成されることにより前記循環流が形成される請求項3に記載の方法。
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JP4577205B2 true JP4577205B2 (ja) | 2010-11-10 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102773048B (zh) * | 2011-05-09 | 2017-06-06 | 波利玛利欧洲股份公司 | 生产环己酮肟的氨肟化反应器 |
CN103551085A (zh) * | 2013-11-08 | 2014-02-05 | 神马实业股份有限公司 | 一种用于环己酮氨肟化反应的催化剂分离装置 |
CN103551087B (zh) * | 2013-11-08 | 2015-11-18 | 神马实业股份有限公司 | 一种用于制备环己酮肟的氨肟化反应系统 |
CN114230482A (zh) * | 2021-09-09 | 2022-03-25 | 浙江吉瑞通新材料有限公司 | 一种环己酮氨肟化生产环已酮肟的方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6046123U (ja) * | 1983-09-07 | 1985-04-01 | 石川島播磨重工業株式会社 | 固液混相流体等を含む液体の反応装置 |
JPS63130575A (ja) * | 1986-11-14 | 1988-06-02 | モンテデイペ・ソチエタ・ペル・アツイオニ | オキシム製造のための接触方法 |
JPH0692922A (ja) * | 1991-01-23 | 1994-04-05 | Enichem Anic Spa | カルボニル化合物の液相アンモオキシム化多段法 |
JPH10113551A (ja) * | 1996-10-15 | 1998-05-06 | Kuraray Co Ltd | 連続反応装置及びそれを用いた生産方法 |
JPH10506837A (ja) * | 1994-10-07 | 1998-07-07 | バイエル・アクチエンゲゼルシヤフト | スラッジ相反応器およびその用途 |
-
2005
- 2005-12-19 JP JP2005364436A patent/JP4577205B2/ja not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6046123U (ja) * | 1983-09-07 | 1985-04-01 | 石川島播磨重工業株式会社 | 固液混相流体等を含む液体の反応装置 |
JPS63130575A (ja) * | 1986-11-14 | 1988-06-02 | モンテデイペ・ソチエタ・ペル・アツイオニ | オキシム製造のための接触方法 |
JPH0692922A (ja) * | 1991-01-23 | 1994-04-05 | Enichem Anic Spa | カルボニル化合物の液相アンモオキシム化多段法 |
JPH10506837A (ja) * | 1994-10-07 | 1998-07-07 | バイエル・アクチエンゲゼルシヤフト | スラッジ相反応器およびその用途 |
JPH10113551A (ja) * | 1996-10-15 | 1998-05-06 | Kuraray Co Ltd | 連続反応装置及びそれを用いた生産方法 |
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